CN101848889B - Alpha-substituted cyclopentanecarbonitriles or cyclohexanecarbonitriles and their use in perfumery - Google Patents
Alpha-substituted cyclopentanecarbonitriles or cyclohexanecarbonitriles and their use in perfumery Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0208—Tissues; Wipes; Patches
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61Q15/00—Anti-perspirants or body deodorants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
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- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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Abstract
The present invention relates to the field of perfumery. More particularly, it concerns alpha-substituted cyclopentanecarbonitriles or cyclohexanecarbonitriles. Said compounds are valuable perfuming ingredients having fruity and/or jasminic odor notes. The present invention also concerns the compositions or articles containing said compound.
Description
Technical field
The present invention relates to field of perfumery.More specifically, it relates to alpha-substitution ring valeronitrile or alpha-substitution cyclohexanenitrile.Described compound is the valuable perfuming component with fruity and/or jasmine smell aromatic.The invention still further relates to and contain described compound compositions or goods.
Background technology
As far as we know, pentamethylene of the present invention or cyclopentene compound are not that prior art is known.Some cyclohexanenitrile derivatives are known in the literature.Really, 2-(5-hexenyl)-cyclohexanenitrile (Organic Letters (2006), 8 (8), 1557-1559), 2-(4-methyl-3-pentenyl)-cyclohexanenitrile, 2-(4-methyl-3-pentenyl)-cyclohexanenitrile and 2-(2-methyl-2-propenyl)-cyclohexanenitrile (Tetrahedron Letters (1978), 28,2461-2464), 2-(1,2-dimethyl-2-propenyl)-cyclohexanenitrile (Journal of Organic Chemistry (1975), 40 (10), 1447-1450) and 2-(1, the 1-dimethyl ethyl)-and cyclohexanenitrile (Canadian Journal of Chemistry (1973), 51 (5), be known 741-747).Yet any organoleptics property of these compounds or The compounds of this invention is not reported or hinted to these prior art documents.They are not also reported or hint that described compound is in any purposes of field of perfumery.
Known in fact structurally very different as the immediate analogue of structure of perfuming component of prior art are because it is ketone.Described compound is alismone, and its organoleptics property with them is disclosed in the Perfume and FlavorChemicals of S.Arctander, 1969, Montclair, and New Jersey, USA is among the N ° 1534.But those skilled in the art can not be as expecting these compounds of perception compound of the present invention and their purposes, because they do not have the carbon atom of equal amts, also because they are connected with different functional groups.
Summary of the invention
We have found unexpectedly that now the compound of general formula (I) can be advantageously used for perfuming component, for example give the smell aromatic of jasmine, fruity (as apricot), lactone and/or celery type,
Wherein a dotted line represents that the place key is singly-bound or two key, and two dotted lines represent that the place key is singly-bound, and n is 0 or 1, R
1Be C
3-C
8Alkyl or alkenyl, and the form of described compound is the mixture of any or they in its diastereomer.
For the sake of clarity, the meaning of saying " wherein a dotted line represents that the place key is singly-bound or two key; two dotted lines represent that the place key is singly-bound " etc. is common implication understood by one of ordinary skill in the art, is carbon-carbon single bond or carbon-carbon double bond by the whole piece key (solid line and dotted line) between the carbon atom of described dotted line connection namely.
According to another implementation of the invention, the compound of general formula (II) can be used as perfuming component,
Wherein n is 0 or 1, R
1Be C
3-C
8Alkyl or alkenyl, the form of described compound are the mixture of any or they in its diastereomer.
Above-mentioned arbitrary embodiment according to the present invention, described general formula (I) or compound (II) are R wherein
1Be C
4-C
8Or C
5-C
7The compound of alkyl.
According to another implementation of the invention, R in the general formula (I)
1The compound that is straight chained alkyl or thiazolinyl can be used as perfuming component.
Above-mentioned arbitrary embodiment according to the present invention, described general formula (I) or compound (II) are 0 compound for n wherein.
According to another embodiment of the invention, described compound (II) is general formula (III) or compound (IV),
R wherein
2Expression C
5-8The alkyl or alkenyl of straight chain or ring-type, R
3Expression C
3-6The alkyl or alkenyl of straight chain or ring-type.
In addition, according to specific implementations of the present invention, below any form in the mixture of these any or they in can its diastereomer as perfuming component: 2-[(2E)-the 2-octenyl] ring valeronitrile, 1,1 '-two (cyclopentyl)-2-nitriles, 1,1 '-two (cyclohexyl)-2-nitriles, 2-propyl group cyclohexanenitrile, 2-allyl group cyclohexanenitrile, 2-heptyl ring valeronitrile or 2-amyl group ring valeronitrile.2-heptyl ring valeronitrile or 2-amyl group ring valeronitrile have represented the embodiment that the present invention values especially.
General formula (I) and (II), (III) or compound (IV) be new compound, therefore be one object of the present invention, except above-mentioned 2-(5-hexenyl)-cyclohexanenitrile, 2-(4-methyl-3-pentenyl)-cyclohexanenitrile, 2-(4-methyl-3-pentenyl)-cyclohexanenitrile, 2-(2-methyl-2-propenyl)-cyclohexanenitrile, 2-(1,2-dimethyl-2-propenyl)-cyclohexanenitrile and 2-(1,1-dimethyl ethyl)-cyclohexanenitrile.
According to the embodiment of the present invention, described new compound is general formula (I) or (II) those, wherein
N is 1 and R
1Be the C except the tertiary butyl
4-C
8Alkyl; Or
N is 0 and R
1Be C
4-C
8Alkyl or alkenyl.
As mentioned above, the common smell type of general formula of the present invention (I) compound comprises jasmine, fruity (as apricot), lactone and/or celery aromatic type.Especially, those of general formula (III) comprise jasmine, apricot and/or lactone aromatic, and those of general formula (IV) comprise celery and/or the fragrance of a flower (as jasmine or rose) aromatic.
As the representative instance of The compounds of this invention, can enumerate 2-heptyl ring valeronitrile.The smell of this compound can be described to have fruity-apricot pericarp (peal), lactone, jasmine smell aromatic, have the cilantro smell.In fact, the whole smell impression of described compound almost is lactone, and this is unexpected for carbonitrile derivatives fully.From the viewpoint of spices, although and important textural difference arranged, also will be with nitrile of the present invention and known spices lactone such as δ-undecalactone and γ-decalactone contrast.Yet nitrile of the present invention still is different from described lactone part and is, it gives aromatic more natural, sweet-smelling, and has jasmine and coriander aromatic, thereby produces the original combination of these features.And nitrile of the present invention demonstrates excellent persistence (substantivity), and with several different application in the lactone enumerated compare better stability, this is always favourable.
When with 2-heptyl ring valeronitrile and known all roads stronger and more multi-substituent ketone (Veloutone, 2,2, the 5-trimethylammonium-5-amyl group-1-cyclopentanone that is widely used in giving jasmine, lactone and fruity aromatic; The source: Firmenich SA) when comparing, compound of the present invention has fruity more lactones and still less-sweet-smelling feature.
As other representative instance of the present invention, can also enumerate 2-amyl group ring valeronitrile.The smell of this compound also can be described to have the aromatic fragrance of a flower-jasmine, that have pungent-celery auxilliary fragrant (side notes), also has the lactone intension of easily being discovered simultaneously.
As other representative instance of the present invention, can also enumerate:
2-[(2E)-and the 2-octenyl] the ring valeronitrile, smell: the feature of apricot, lactone;
1,1 '-two (cyclopentyl)-2-nitriles, smell: fragrance of a flower jasmine, celery, lactone aromatic;
2-propyl group cyclohexanenitrile, smell: fragrance of a flower jasmine, celery, lactone, peppermint aromatic;
1,1 '-two (cyclohexyl)-2-nitriles, smell: rose, phenylethyl alcohol (phenylethylol), Chinese cassia tree, celery aromatic.
Now, as mentioned above, prior art known as perfuming component very different on structure and organoleptic feature with the immediate analogue of structure nitrile of the present invention.
When nitrile of the present invention is compared with the prior art, The compounds of this invention since lack or do not have tangible, not mature/draft smell aromatic and owing to have a lactone and/or the celery feature be different from them.
Especially, when the smell of 2-heptyl ring valeronitrile and alismone compare, compound of the present invention since have lactone, apricot-peach and coconut smell aromatic (alismone is unexistent), and because the smell aromatic feature of the not mature-draft/acid of shortage alismone is distinguished itself.
Described difference causes The compounds of this invention to be applicable to different purposes separately with the prior art compound, namely gives different organoleptic impressions.
As mentioned above, the present invention relates to general formula (I) compound as the purposes of perfuming component.In other words, it relates to a kind ofly gives, improves, promotes or change perfume composition or the method for the odor property of perfumed article, and this method comprises the compound that adds at least a general formula (I) of significant quantity to described composition or goods." purposes of the compound of general formula (I) " also it must be understood that purposes into any composition of inclusion compound (I) at this, and it can be advantageously used in perfume industry as activeconstituents.
The described composition that in fact can be advantageously used for perfuming component also is one object of the present invention.
Therefore, another object of the present invention is a kind of perfume composition, and it comprises:
I) as the compound of the general formula (I) of at least a as above arbitrary embodiment definition of perfuming component;
The ii) at least a composition that is selected from fragrance carrier and perfumery base; With
The iii) at least a spices adjuvant of optional selection.
" fragrance carrier " represented to be actually neutral material from the viewpoint of spices at this, namely significantly do not change the organoleptics property of perfuming component.Described carrier can be liquid or solid.
Can enumerate emulsification system as limiting examples as liquid vehicle, i.e. solvent and surfactant system, or be generally used for the solvent of spices.Being generally used for the character of solvent of spices and the detailed description of type is impossible exhaustive.Yet, can enumerate as the solvent of limiting examples such as dipropylene glycol, diethyl phthalate, Isopropyl myristate, peruscabin, 2-(2-ethoxy ethoxy)-1-ethanol or ETHYL CTTRATE, they are the most normally used.
Can enumerate absorption glue or polymkeric substance as limiting examples as solid carrier, or also have encapsulating material.The example of this class material can comprise into wall material and plastification material, as monose, disaccharides or trisaccharide, and natural or treated starch, hydrocolloid, derivatived cellulose, polyvinyl acetate, polyvinyl alcohol, protein or pectin, or in addition at reference such as H.Scherz, Hydrorolloids:Stabilisatoren, Dickungs-undGehermittel in Lebensmittel, Band 2 der Schriftenreihe Lebensmittelchemie
Behr ' s VerlagGmbH ﹠amp; Co., hamburger, the material of enumerating in 1996.Sealing is to well known to a person skilled in the art technology, and can be undertaken by for example using as spraying drying, agglomeration or the technology extruded in addition; Or form by comprising that cohesion and the coating of complex coacervation technology are sealed.
" perfumery base " comprises the composition that at least a perfuming furtherance divides in this expression.
It is not general formula (I) compound that described perfuming furtherance divides.In addition, " perfuming furtherance branch " represents a kind of compound at this, and this compound is used for perfuming preparation or composition to give a kind of pleasant sensation.In other words, consider as a kind of perfuming material that such furtherance branch is necessary for those skilled in the art's cognition can give or change the smell of composition in positive or pleasant mode, and is not only to have smell.
Character and type that the perfuming furtherance that exists in the base-material divides do not guarantee more detailed description at this, it under any circumstance can not be exhaustive, and those skilled in the art can be on its general knowledge bases and selected them according to the purposes of expection or application and required sensory effects.On ordinary meaning, these perfuming furtherances belong to following multiple chemical classification: alcohol, aldehyde, ketone, ester, ether, acetic ester, nitrile, terpenoid, nitrogenous or sulfur heterocyclic compound and essential oil, and described perfuming furtherance branch can be natural or synthetic source.In any case dividing, many these perfuming furtherances in reference, list, books S.Arctander for example, Perfume and Flavor Chemicals, 1969, Montclair, the New Jersey, USA, or its nearlyer version, or other works of similar kind, and the abundant patent documentation of field of perfumery.Be understood that also it also can be the known compound that discharges all kinds fragrance compound in a controlled manner that described furtherance divides.
For the composition that comprises fragrance carrier and perfumery base, except previously described other suitable flavorants carrier those also can be alcohol, water/alcohol mixture, limonene or other terpenes, isoparaffin as with trade mark Isopar
(source: known those Exxon Chemical), or glycol ethers and glycol ether-ether are as with trade mark Dowanol
(source: known those DowChemical Company).
" spices adjuvant " can give the composition of the benefit of extra increase such as color, specific photostabilization, chemical stability etc. in this expression.Being generally used for the character of adjuvant of perfuming base-material and the detailed description of type is impossible exhaustive, but what must mention is that described composition is well known to a person skilled in the art.
The present composition of being formed by compound and at least a fragrance carrier of at least a general formula (I), and the perfume composition that comprises at least a spices adjuvant of the compound of at least a general formula (I), at least a fragrance carrier, at least a perfumery base and optional selection, all represent specific implementations of the present invention.
Mention usefully that at this possibility that contains more than the compound of a kind of general formula (I) is important in above-mentioned composition, this is because temper, the perfume of the smell tune (tonality) that it makes the perfumer to prepare to have all cpds of the present invention, thereby produces the new tool that is used for their work.
Preferably, any mixture that is directly obtained by chemosynthesis, for example without enough purifying, wherein compound of the present invention can all can not be thought perfume composition of the present invention as initial, centre or final product.
In addition, can be advantageously used in all modern field of perfumery actively to give or to change the smell of the consumer's goods of compound (I) as described in wherein add as the compound of the general formula (I) of perfuming component or composition as above arbitrary embodiment is disclosed.Therefore, the perfumed article that comprises following material also is purpose of the present invention:
I) compound of at least a general formula as defined above (I) is as perfuming component; With
Ii) a kind of consumer product base.
What for clarity sake, must mention is that " consumer product base " is at this expression consumer's goods compatible with perfuming component.In other words, perfumed article of the present invention comprises the function preparaton, and optional selection corresponding to the extra beneficial agent of the consumer's goods (as washing composition or air freshener) and at least a The compounds of this invention of sense of smell significant quantity.
The character of the component of the consumer's goods and type do not guarantee more detailed description at this, and it in no case can be exhaustive, those skilled in the art can be on the basis of general knowledge and according to the character of described product and required effect selection they.
The example of suitable consumer product base comprises common all other goods in solid or liquid washing agent and fabric softener and the spices, be perfume, Gu Longshui or aftershave lotion, perfumed soap, bath salt, bath oil, bath oil or body wash, health product or hair care product such as shampoo, body care product, reodorant or antiperspirant, air freshener and cosmetic formulations.As washing composition, the application of expection is used for textiles, plate or crust as hope and handles as being used for washing or cleaning detergent composition or the cleaning product on various surfaces, and no matter it is want for family or industrial application.Other perfumed article be fabric refreshers, flatiron water, paper, Wiping article or SYNTHETIC OPTICAL WHITNER.
Some above-mentioned consumer product base may represent the corrosive medium of The compounds of this invention, and making may be for example by sealing the protection The compounds of this invention to avoid causing premature decomposition.
The ratio that compound of the present invention can be joined various said products or composition changes in wide numerical range.When compound of the present invention mixed with the perfuming furtherance branch, solvent or the additive that are generally used for this area, these numerical value depended on character and required sensory effect and the character that furtherance divides in given base-material of wanting perfumed article.
For example, under the situation of perfume composition, the typical concentration of The compounds of this invention is about 0.01%～10% weight or even more based on the composition weight that they is added wherein.When these compounds being added perfumed article, with respect to the percentage ratio of product weight, can use the concentration that is lower than these, according to appointment 0.01%～5% weight.
Description of drawings
Fig. 1 represents by the 2-heptyl ring valeronitrile of embodiment 1 method preparation
1The H-NMR collection of illustrative plates.
Embodiment
Embodiment
To the present invention be described in further detail by following embodiment now, wherein abbreviation has a common implication of this area, temperature with degree centigrade (℃) expression, the NMR spectroscopic data is at CDCl
3If the instrument of employing 360 or 400MHz is right in (not explanation in addition)
1H and
13The record of C, chemical shift δ are represented with ppm as standard substance with TMS, express coupling constant J with Hz.
Embodiment 1
Synthesizing of general formula (I) compound
Synthesizing of 2-heptyl ring valeronitrile
The tolylsulfonyl ylmethyl isonitrile of 27.6g and the alismone of 20g are dissolved in 1 of 400ml, in 2-glycol dimethyl ether and the 10ml ethanol.This solution is cooled to 0 ℃ with ice bath, and in 1 hour, keeps adding under 0～10 ℃ the temperature 29g's
tBuOK.After reaction is finished, reaction mixture poured in the water and with hexanaphthene extract.Wash organic layer with water 3 times up to pH value neutrality.With ball to ball distillation (150 ℃/0.06mbar) purifying obtains the pure 2-heptyl ring valeronitrile of 13.4g.
13C-NMR：14.10(q)；22.68(t)；23.18(t)；24.21(t)；28.09(t)；28.53(t)；29.22(t)；29.25(t)；29.67(t)；30.55(t)；30.60(t)；30.81(t)；31.83(t)；31.85(t)；31.87(t)；32.17(t)；33.95(d)；34.40(d)；34.70(t)；43.00(d)；45.94(d)；121.45(s)；123.26(s)。
IR：2955，2924，2855，2235，1626，1455，1377，1304，1125，911，889，723cm
-1。
Synthesizing of 2-amyl group ring valeronitrile
The tolylsulfonyl ylmethyl isonitrile of 27.6g and the 2-amyl group cyclopentanone of 17g are dissolved in 1 of 400ml, in 2-glycol dimethyl ether and the 10ml ethanol.This solution is cooled to 0 ℃ with ice bath, and in 1 hour, keeps adding under 0～10 ℃ the temperature 29g's
tBuOK.After reaction is finished, reaction mixture poured in the water and with hexanaphthene extract.Wash organic layer with water 3 times up to pH value neutrality.With ball to ball distillation (130 ℃/0.06mbar) purifying obtains the pure 2-amyl group ring valeronitrile of 10.7g.
13C-NMR：14.04(q)；22.56(t)；22.58(t)；23.17(t)；24.21(t)；27.74(t)；28.17(t)；30.54(t)；30.60(t)；30.80(t)；31.82(t)；31.88(t)；32.11(t)；33.93(d)；34.40(d)；34.64(t)；43.00(d)；45.93(d)；121.48(s)；123.29(s)。
Use the experimental procedure (identical mole dosage and purification procedures) identical with above two embodiment, also obtain following compound:
2-[(2E)-and the 2-octenyl] the ring valeronitrile
By 2-[(2E)-the 2-octenyl] cyclopentanone is synthetic, and productive rate is 48% (suitable/inverse proportion is 50/50) behind the sharp separation chromatogram purification
13C-NMR：14.07(q)，22.53(t)，23.08(t)，24.21(t)，29.13(t)，29.17(t)，30.19(t)，30.46(t)，30.77(t)，31.19(t)，31.40(t)，31.41(t)，32.52(t)，32.55(t)，33.39(d)，33.74(d)，35.16(t)，37.11(t)，43.22(d)，45.66(d)，121.32(s)，123.08(s)，126.72(d)，127.50(d)，132.85(d)，133.49(d)
1,1 '-two (cyclopentyl)-2-nitriles
Synthetic by 2-(cyclopentyl)-cyclopentanone, productive rate is 60% (suitable/inverse proportion is 50/50) behind the sharp separation chromatogram purification
13C-NMR：23.17(t)，24.73(t)，25.01(t)，25.21(t)，25.24(t)，25.40(t)，30.02(t)，30.72(t)，31.15(t)，31.19(t)，31.39(t)，31.55(t)，32.06(t)，32.14(t)，32.21(d)，33.99(d)，43.19(d)，45.42(d)，50.03(d)，50.98(d)，121.71(s)，123.79(s)
2-allyl group cyclohexanenitrile
Synthetic by 2-allyl group pimelinketone, productive rate is 60% (suitable/inverse proportion is 50/50) behind the sharp separation chromatogram purification
13C-NMR：22.25(t)，24.88(t)，24.91(t)，25.36(t)，28.89(t)，28.97(t)，29.93(t)，30.25(t)，32.39(d)，33.92(d)，38.62(d)，38.75(t)，39.13(t)，39.56(d)，117.34(t)，117.66(t)，120.39(s)，122.08(s)，134.71(d)，135.30(d)；
2-propyl group cyclohexanenitrile
Synthetic by 2-propyl group pimelinketone, productive rate is 60% (suitable/inverse proportion is 50/50) behind the sharp separation chromatogram purification
13C-NMR：14.07(q)，14.15(q)，19.40(t)，19.75(t)，22.40(t)，24.98(t)，25.05(t)，25.38(t)，29.01(t)，29.05(t)，30.16(t)，30.54(t)，32.92(d)，34.97(d)，36.86(t)，36.92(t)，38.48(d)，39.63(d)，120.69(s)，122.44(s)
1,1 '-two (cyclohexyl)-2-nitriles
Synthetic by 2-(cyclohexyl)-pimelinketone, productive rate is 20% (suitable/inverse proportion is 50/50) behind the sharp separation chromatogram purification
13C-NMR：22.29(t)，25.26(t)，25.35(t)，25.82(t)，26.15(t)，26.19(t)，26.41(t)，26.43(t)，26.59(t)，26.64(t)，26.77(t)，26.97(t)，29.45(t)，30.36(t)，30.53(t)，30.63(t)，31.34(t)，32.17(d)，40.27(d)，40.44(d)，44.51(d)，45.31(d)，120.99(s)，122.32(s)；
Embodiment 2
The preparation of perfume composition
By following composition being mixed to prepare the fragrance of a flower-fruity perfume:
*In dipropylene glycol
1) ten dihydros-3a, 6,6,9a-tetramethyl--naphtho-[2,1-b] furans; Source: FirmenichSA, Geneva, Switzerland
2) pentadecane lactone; Source: Firmenich SA, Geneva, Switzerland
3) source: Firmenich SA, Geneva, Switzerland
4) isomer mixture of methylionone, source: Firmenich SA, Geneva, Switzerland
5) methyl dihydrojasmonate, source: Firmenich SA, Geneva, Switzerland
6) 3-(4-tert-butyl-phenyl)-2 methyl propanal, source: Givaudan-Roure SA, Vernier, Switzerland
7) acetic acid 4-(1,1-dimethyl ethyl)-1-cyclohexyl, source: Firmenich SA, Geneva, Switzerland
8) the acetic acid 2-tertiary butyl-1-cyclohexyl, source: International Flavors ﹠amp; Fragrances, USA
9) vertofix coeur, source: International Flavors ﹠amp; Fragrances, USA
10) banana aldehyde base-material, source: Firmenich SA, Geneva, Switzerland
50 weight part 2-heptyl ring valeronitriles are joined in the above-mentioned temper, give the latter with pleasant apricot, lactone and the fragrance of the fragrance of a flower-jasmine aromatic slightly.
When replacing The compounds of this invention to add the lactone of same consumption, the perfume that obtains has the smell of food, and this temper smell with expection is not inconsistent.
When replacing The compounds of this invention to add the alismone of same consumption, because the existence of inappropriate not mature aromatic and more weak fruity and lack the lactone aromatic obtain stronger perfume.
Embodiment 3
The preparation of perfume composition
By following composition being mixed to prepare fruity-jasmine temper:
*In dipropylene glycol
1) source: Firmenich SA, Geneva, Switzerland
2) pentadecane lactone; Source: Firmenich SA, Geneva, Switzerland
3) tetrahydrochysene-2-isobutyl--4-methyl-4 (2H)-Pai Lannuo oil; Source: FirmenichSA, Geneva, Switzerland
4) methyl dihydrojasmonate, source: Firmenich SA, Geneva, Switzerland
5) banana aldehyde base-material, source: Firmenich SA, Geneva, Switzerland
30 weight part 2-heptyl ring valeronitriles are joined in above-mentioned single fruity-jasmine temper, strengthened fruity and fragrance by giving very natural apricot pericarp (peal) aromatic.
When replacing The compounds of this invention to add the alismone of same consumption, because the existence of inappropriate not mature aromatic and more weak fruity and lack the lactone aromatic obtain stronger perfume.
Embodiment 4
The preparation of perfume composition
By following composition being mixed to prepare the fragrance of a flower-jasmine temper:
*In dipropylene glycol
1) source: Firmenich SA, Geneva, Switzerland
2) isomer mixture of methylionone, source: Firmenich SA, Geneva, Switzerland
3) methyl dihydrojasmonate, source: Firmenich SA, Geneva, Switzerland
4) pentadecane lactone; Source: Firmenich SA, Geneva, Switzerland
5) suitable-7-is right
Alkanol
30 weight part 2-heptyl ring valeronitriles are joined in the above-mentioned temper, make it show to such an extent that more fragrantly strengthened the jasmine aromatic in more natural, and in whole evaporation process, prolonging this effect.
When replacing The compounds of this invention to add the alismone of same consumption, because the existence of inappropriate not mature aromatic and more weak fruity and lack the lactone aromatic obtain stronger perfume.
Claims (9)
1. the compound of a general formula (I) is as the purposes of perfuming component,
Wherein a dotted line represents that the place key is singly-bound or two key, and two dotted lines represent that the place key is singly-bound, and n is 0 or 1, R
1Be C
3-C
8Alkyl or alkenyl.
2. according to the purposes of claim 1, it is characterized in that described compound (I) is the compound of general formula (II),
Wherein n is 0 or 1, R
1Be C
3-C
8Alkyl or alkenyl.
3. according to the purposes of claim 1 or 2, it is characterized in that R
1Be C
4-C
8Alkyl.
4. according to the purposes of claim 1 or 2, it is characterized in that n is 0.
5. according to the purposes of claim 1 or 2, the compound that it is characterized in that general formula (I) is 2-heptyl ring valeronitrile or 2-amyl group ring valeronitrile.
6. perfume composition comprises:
I) compound of at least a general formula as each definition in the claim 1 ~ 5 (I) is as perfuming component;
The ii) at least a composition that is selected from fragrance carrier and perfumery base; With
The iii) at least a spices adjuvant of optional selection.
7. perfumed article comprises:
I) compound of at least a general formula as each definition in the claim 1 ~ 5 (I) is as perfuming component; With
Ii) a kind of consumer product base, this consumer product base is solid or liquid washing agent, fabric softener, hair care product, body care product, reodorant, air freshener, cosmetic formulations, fabric refreshers, flatiron water, paper or SYNTHETIC OPTICAL WHITNER.
8. the perfumed article according to claim 7 is characterized in that this consumer product base is Gu Longshui, perfumed soap, bath salt, bath oil, bath oil or body wash, shampoo or antiperspirant.
9. the perfumed article according to claim 7 is characterized in that this consumer product base is perfume or aftershave lotion.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2007054516 | 2007-11-07 | ||
| IBPCT/IB2007/054516 | 2007-11-07 | ||
| PCT/IB2008/054577 WO2009060378A2 (en) | 2007-11-07 | 2008-11-04 | Alpha-substituted cyclopentanecarbonitriles or cyclohexanecarbonitriles and their use in perfumery |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101848889A CN101848889A (en) | 2010-09-29 |
| CN101848889B true CN101848889B (en) | 2013-07-17 |
Family
ID=40545753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008801149567A Expired - Fee Related CN101848889B (en) | 2007-11-07 | 2008-11-04 | Alpha-substituted cyclopentanecarbonitriles or cyclohexanecarbonitriles and their use in perfumery |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8003084B2 (en) |
| EP (1) | EP2217563B1 (en) |
| CN (1) | CN101848889B (en) |
| WO (1) | WO2009060378A2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX337560B (en) * | 2010-11-10 | 2016-03-10 | Basf Se | Fragrance compositions comprising special mixtures of diastereomers of 2-isobutyl-4-methyl-tetrahydro-2h-pyran-4-ol. |
| US9708568B2 (en) * | 2014-05-06 | 2017-07-18 | The Procter & Gamble Company | Fragrance compositions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146507A (en) * | 1976-10-26 | 1979-03-27 | Polak's Frutal Works, Inc. | Novel cyclohexene-3-nitriles in perfume compositions |
-
2008
- 2008-11-04 US US12/738,721 patent/US8003084B2/en active Active
- 2008-11-04 CN CN2008801149567A patent/CN101848889B/en not_active Expired - Fee Related
- 2008-11-04 WO PCT/IB2008/054577 patent/WO2009060378A2/en active Application Filing
- 2008-11-04 EP EP08847739A patent/EP2217563B1/en not_active Not-in-force
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146507A (en) * | 1976-10-26 | 1979-03-27 | Polak's Frutal Works, Inc. | Novel cyclohexene-3-nitriles in perfume compositions |
Non-Patent Citations (7)
| Title |
|---|
| Alkenenitriles: Conjugate Additions of Alkyl Iodides with a Silica-Supported Zinc-Copper Matrix in Water;Fraser F. Fleming, et al.;《J. Org. Chem.》;20070808;第72卷(第18期);6961-6969 * |
| Fraser F. Fleming, et al..Alkenenitriles: Conjugate Additions of Alkyl Iodides with a Silica-Supported Zinc-Copper Matrix in Water.《J. Org. Chem.》.2007,第72卷(第18期),6961-6969. |
| George Majetich et al..A General Allylation Procedure Using Trimet hylallylsilane and Fluoride Catalysis.《J. Org. Chem.》.1986,第51卷(第10期),1745-1753. * |
| M. Julia et al..Cyclisation radicalaire. II. cyclisation d’esters alpha-cyanes epsylion-èthylènipues en esters.《Bulletin de la societe chimique de france》.1964,第5卷1109-1116. * |
| Synthesis and Reactivity of Open-Chain and Cyclic 2-Cvano Zinc and Copper Organometallics;Tahir N. Majid et al.;《Tetrahedron Letters》;19891231;第30卷(第38期);5069-5072 * |
| Tahir N. Majid et al..Synthesis and Reactivity of Open-Chain and Cyclic 2-Cvano Zinc and Copper Organometallics.《Tetrahedron Letters》.1989,第30卷(第38期),5069-5072. |
| Y. Zhang et al..Carbon-Carbon Bond Formation via Opening of Epoxysilanes with Organometals Containing Lithium and Copper.《J. Org. Chem.》.1989,第54卷2043-2044. * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009060378A3 (en) | 2009-07-23 |
| WO2009060378A2 (en) | 2009-05-14 |
| EP2217563A2 (en) | 2010-08-18 |
| US8003084B2 (en) | 2011-08-23 |
| CN101848889A (en) | 2010-09-29 |
| EP2217563B1 (en) | 2013-01-30 |
| US20100247467A1 (en) | 2010-09-30 |
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